Dispersible pesticidal compositions

ABSTRACT

Soluble granule pesticidal compositions comprise Flonicamid, a dispersant, and a wetting agent are disclosed.

This application claims the benefit of U.S. Provisional Application No.60/562,071, filed Apr. 14, 2004.

FIELD OF THE INVENTION

The present invention relates to pesticidal compositions. In particular,the invention provides a soluble granule formulation of Flonicamid, awater-soluble pesticide, which is easily dispersed in an aqueous medium.

BACKGROUND OF THE INVENTION

To enable the efficient elimination or controlling of unwanted pests, itis desirable to use effective chemical pesticides on these unwantedpests. Soluble granule formulations containing water-soluble pesticidesare desirable in agricultural and related endeavors due to ease ofhandling and the elimination of organic solvents, which can be costlyand dangerous to the environment. Safety, specifically eye irritation,caused by solvents, dispersants, clays and wetting agents in traditionalformulations are also of concern. In addition, the process used to makethe soluble granule formulation can be conducted in relatively simpleequipment using relatively simple process steps.

The formulation of soluble granule pesticides has been disclosed in theprior art, for example in U.S. Pat. No. 6,387,388 (Misselbrook et al.).Challenges in formulating a soluble granule of a water-soluble pesticideinclude the requirements that the final product successfully achieves(a) good dispersibility/solubility in an aqueous medium and (b) chemicalstability once dispersed.

Good dispersibility/solubility in an aqueous medium is important in asoluble granule formulation since ineffective mixing of the pesticideinto solution can result in reduced or inconsistent efficacy and,ultimately, costly returns of product and loss of sales. Chemicaldegradation is also important because there may be no physical sign ofthe degradation and resultant loss of efficacy until used on a pest.Examples of problematic chemical degradation include hydrolysis,oxidation, dehalogenation and bond cleavage.

SUMMARY OF THE INVENTION

The present invention is directed to a soluble granule compositioncomprising Flonicamid, a dispersant, and a wetting agent. This solublegranule composition has improved dispersibility/solubility as comparedto other formulations.

DETAILED DESCRIPTION OF THE INVENTION

As used in this specification and unless otherwise indicated the term“Flonicamid” refers to N-cyanomethyl-4-trifluoromethyl nicotinamide, orsalts thereof. The term “pesticide” refers to a molecule or combinationof molecules that repels, retards, or kills pests, such as, but notlimited to, deleterious or annoying insects, weeds, worms, fungi,bacteria, and the like, and can be used for crop protection, edificeprotection, turf protection, or protection of a person; pesticide asused herein includes, but is not limited to, herbicides, insecticides,acaricides, fungicides, nematicides, ectoparasiticides, and growthregulators, either used to encourage growth of a desired plant speciesor retard growth of an undesired pest.

The modifier “about” is used herein to indicate that certain preferredoperating ranges, such as ranges for molar ratios for reactants,material amounts, and temperature, are not fixedly determined. Themeaning will often be apparent to one of ordinary skill. For example, arecitation of a temperature range of about 120° C. to about 135° C. inreference to, for example, an organic chemical reaction would beinterpreted to include other like temperatures that can be expected tofavor a useful reaction rate for the reaction, such as 105° C. or 150°C. Where guidance from the experience of those of ordinary skill islacking, guidance from the context is lacking, and where a more specificrule is not recited below, the “about” range shall be not more than 10%of the absolute value of an end point or 10% of the range recited,whichever is less.

As used in this specification and unless otherwise indicated thesubstituent terms “alkyl”, “cycloalkyl”, “alkoxy”, “aryloxy”, and“alkoxyarylamino”, used alone or as part of a larger moiety, includesstraight or branched chains of at least one or two carbon atoms, asappropriate to the substituent, and preferably up to 20 carbon atoms,more preferably up to ten carbon atoms, most preferably up to sevencarbon atoms. “Halogen” or “halo” refers to fluorine, bromine, iodine,or chlorine. “Aryl” refers to an aromatic ring structure having 5 to 10carbon atoms.

The term “ambient temperature” as utilized herein shall mean anysuitable temperature found in a laboratory or other working environment,and is generally not below about 15° C. nor above about 30° C.

The present invention is directed to a soluble granule compositioncomprising Flonicamid, a dispersant, and a wetting agent. The inventioncan further comprise a water-soluble carrier.

Flonicamid can be present in a concentration of from 1% by weight to 94%by weight, more particularly 45% by weight to 55% by weight, based uponthe total weight of all components in the composition.

The dispersant can be selected from the group consisting of sodium alkylnaphthalene sulfonate formaldehyde condensate, modified acrylatecopolymer (sodium salt), alkyl naphthalene sulfonate salts and dodecylbenzene sulfonate (Na) salt. Preferably, the dispersant is sodium alkylnaphthalene sulfonate formaldehyde condensate. The dispersant can bepresent in a concentration of from 0.5% by weight to 20% by weight, moreparticularly 2% by weight to 6% by weight, based upon the total weightof all components in the composition.

The wetting agent can be selected from the group consisting of a mixtureof sodium dioctylsufosuccinate and sodium benzoate wherein the sodiumdioctylsufosuccinate is up to 85 weight percent, polyalkylencoxidemodified heptamethyl trisiloxane, alkyloxypolyethylene glycol methylether and alcohol (C8-C16) ethoxylates with 3-20 moles of ethyleneoxide. Preferably, the wetting agent is a mixture of sodiumdioctylsufosuccinate and sodium benzoate wherein the sodiumdioctylsufosuccinate is present in a concentration up to 85 weightpercent. The wetting agent can be present in a concentration of from0.1% by weight to 20% by weight, more particularly 0.5% by weight to 3%by weight, based upon the total weight of all components in thecomposition.

The water-soluble carrier can be selected from the group consisting oflactose, sucrose, glucose, starch, sodium tripolyphosphate andwater-soluble salts. Preferably, the water-soluble carrier is lactose.The water-soluble carrier can be present in a concentration of from0.001% by weight to 97% by weight, more particularly 35% by weight to45% by weight, based upon the total weight of all components in thecomposition.

Another embodiment of the present invention is a soluble granulecomposition comprising Flonicamid; a dispersant selected from the groupconsisting of sodium alkyl naphthalene sulfonate formaldehydecondensate, modified acrylate copolymer (sodium salt), alkyl naphthalenesulfonate salts and dodecyl benzene sulfonate (Na) salt; a wetting agentselected from the group consisting of a mixture of sodiumdioctylsufosuccinate and sodium benzoate wherein the sodiumdioctylsufosuccinate is present in a concentration up to 85 weightpercent, polyalkylencoxide modified heptamethyl trisiloxane,alkyloxypolyethylene glycol methyl ether and alcohol (C8-C16)ethoxylates with 3-20 moles of ethylene oxide; and a water-solublecarrier selected from the group consisting of lactose, sucrose, glucose,starch, sodium tripolyphosphate and water-soluble salts.

Another embodiment of the present invention is a soluble granulecomposition comprising from 1% to 94% of Flonicamid, from 0.5% to 20% ofsodium alkyl naphthalene sulfonate formaldehyde condensate, from 0.1% to20% of a mixture of sodium dioctylsufosuccinate and sodium benzoatewherein the sodium dioctylsufosuccinate is present in a concentration upto 85%, and from 0.001% to 97% of lactose, wherein all % are % by weightbased upon the total weight of all components in the composition.

Yet another embodiment of the present invention is a soluble granulecomposition comprising from 25% to 88% of Flonicamid, from 0.5% to 20%of sodium alkyl naphthalene sulfonate formaldehyde condensate, from 0.4%to 5.0% of a mixture of sodium dioctylsufosuccinate and sodium benzoatewherein the sodium dioctylsufosuccinate is present in a concentration upto 85%, and from 6% to 70% of lactose, wherein all % are % by weightbased upon the total weight of all components in the composition.

Yet another embodiment of the present invention is a soluble granulecomposition comprising from 45% to 55% of Flonicamid, from 2% to 6% ofsodium alkyl naphthalene sulfonate formaldehyde condensate, from 0.5% to3% of a mixture of sodium dioctylsufosuccinate and sodium benzoatewherein the sodium dioctylsufosuccinate is present in a concentration upto 85%, and from 35% to 45% of lactose, wherein all % are % by weightbased upon the total weight of all components in the composition.

The composition may further comprise an anti-foam agent and/or ananti-bacteria agent.

The present invention also encompasses a method of controlling unwantedpests, comprising applying to an area infested with such pests aneffective amount of the soluble granule composition, discussed above, inan aqueous solvent.

The present invention also encompasses a process for preparing thesoluble granule composition comprising a) forming a mixture ofFlonicamid, a dispersant, a wetting agent and, optionally, awater-soluble carrier; b) kneading the mixture; c) extruding the kneadedmixture from step b); and d) drying the extruded mixture from step c).Preferably, the process further comprises milling the mixture prior tokneading.

The pesticidal compositions of the present invention are furtherillustrated by the examples below. Flonicamid used in all examplescontains 97% active ingredient. The examples serve only to illustratethe invention and should not be interpreted as limiting since furthermodifications of the disclosed invention will be apparent to thoseskilled in the art. All such modifications are deemed to be within thescope of the invention as defined in the claims.

In the examples below, testing to demonstrate thedispersibility/solubility of the composition was carried out in thefollowing manner: 1) At ambient temperature, 1.0 gram of the compositionprepared in the example was added to 100 ml of water in a cylinder ofappropriate size; 2) the cylinder was repeatedly inverted 180 degrees toeffect dispersion/solution of the composition into the water; 3) thenumber of inversions required for full dispersion/solution to a clearstate was determined visually and recorded. The results of these testsare presented in each example.

EXAMPLE 1

This example illustrates the preparation of a 50SG composition(Composition A) of the present invention.

A mixture of 52.0 grams of Flonicamid, 5.0 grams of sodiumalkylnaphthalene sulfonate formaldehyde condensate, 1.0 gram of acombination of sodium dioctylsufosuccinate and sodium benzoate (AerosolOTB available from Cytec Industries, Inc. in West Paterson, N.J.) and42.0 grams of lactose were combined and agitated under high shear. Tothis mixture was added 14.0 grams of water and then the mixture waskneaded in a Hobart mixer for about 2 minutes. The kneaded mixture wasthen extruded in a Fuji Paudal DGL-1 using a dome with 0.8-millimeterapertures. The resultant product was then dried at 60° C. with 80%airflow for 10 to 15 minutes until the moisture content of the productwas less than 1%.

Composition A required 3 inversions for full dispersion into a clearsolution.

EXAMPLE 2

This example illustrates the preparation of a 50SG composition(Composition B) of the present invention.

A mixture of 52.0 grams of Flonicamid, 5.0 grams of sodiumalkylnaphthalene sulfonate formaldehyde condensate, 1.0 gram of acombination of sodium dioctylsufosuccinate and sodium benzoate (AerosolOTB available from Cytec Industries, Inc. in West Paterson, N.J.) and42.0 grams of ammonium sulfate were combined and agitated under highshear. To this mixture was added 14.0 grams of water and then themixture was kneaded in a Hobart mixer for about 2 minutes. The kneadedmixture was then extruded in a Fuji Paudal DGL-1 using a dome with0.8-millimeter apertures. The resultant product was then dried at 60° C.with 80% airflow for 10 to 15 minutes until the moisture content of theproduct was less than 1%.

Composition B required 8 inversions for full dispersion into a clearsolution.

EXAMPLE 3

This example illustrates the preparation of a 50SG composition(Composition C) of the present invention.

A mixture of 52.0 grams of Flonicamid, 4.0 grams of modified acrylatecopolymer (sodium salt), 1.0 gram of a combination of sodiumdioctylsufosuccinate and sodium benzoate (Aerosol OTB available fromCytec Industries, Inc. in West Paterson, N.J.) and 43.0 grams of sodiumtripolyphosphate were combined and agitated under high shear. To thismixture was added 14.0 grams of water and then the mixture was kneadedin a Hobart mixer for about 2 minutes. The kneaded mixture was thenextruded in a Fuji Paudal DGL-1 using a dome with 0.8-millimeterapertures. The resultant product was then dried at 60° C. with 80%airflow for 10 to 15 minutes until the moisture content of the productwas less than 1%.

Composition C required 7 inversions for full dispersion into a clearsolution.

EXAMPLE 4

This example illustrates the preparation of a 24SG composition(Composition D) of the present invention.

A mixture of 25.0 grams of Flonicamid, 5.0 grams of sodiumalkylnaphthalene sulfonate formaldehyde condensate, 0.5 gram of acombination of sodium dioctylsufosuccinate and sodium benzoate (AerosolOTB available from Cytec Industries, Inc. in West Paterson, N.J.), 68.45grams of lactose, 1.0 gram of an anti-bacteria agent (Dowcide Aavailable from Dow Chemical Company in Midland, Mich.) and 0.05 gram ofan anti-foam agent were combined and agitated under high shear. To thismixture was added 13.0 grams of water and then the mixture was kneadedin a Hobart mixer for about 2 minutes. The kneaded mixture was thenextruded in a Fuji Paudal DGL-1 using a dome with 0.8-millimeterapertures. The resultant product was then dried at 60° C. with 80%airflow for 10 to 15 minutes until the moisture content of the productwas less than 1%.

Composition D required 5 inversions for full dispersion into a clearsolution.

EXAMPLE 5

This example illustrates the preparation of a 24SG composition(Composition E) of the present invention.

A mixture of 25.0 grams of Flonicamid, 5.0 grams of sodiumalkylnaphthalene sulfonate formaldehyde condensate, 0.5 gram of acombination of sodium dioctylsufosuccinate and sodium benzoate (AerosolOTB available from Cytec Industries, Inc. in West Paterson, N.J.) and69.5 grams of lactose were combined and agitated under high shear. Tothis mixture was added 13.0 grams of water and then the mixture waskneaded in a Hobart mixer for about 2 minutes. The kneaded mixture wasthen extruded in a Fuji Paudal DGL-1 using a dome with 0.8-millimeterapertures. The resultant product was then dried at 60° C. with 80%airflow for 10 to 15 minutes until the moisture content of the productwas less than 1%.

Composition E required 3 inversions for full dispersion into a clearsolution.

EXAMPLE 6

This example illustrates the preparation of an 85SG composition(Composition F) of the present invention.

A mixture of 87.6 grams of Flonicamid, 5.0 grams of sodiumalkylnaphthalene sulfonate formaldehyde condensate, 1.0 gram of acombination of sodium dioctylsufosuccinate and sodium benzoate (AerosolOTB available from Cytec Industries, Inc. in West Paterson, N.J.) and6.4 grams of lactose were combined and agitated under high shear. Tothis mixture was added 15.0 grams of water and then the mixture waskneaded in a Hobart mixer for about 2 minutes. The kneaded mixture wasthen extruded in a Fuji Paudal DGL-1 using a dome with 0.8-millimeterapertures. The resultant product was then dried at 60° C. with 80%airflow for 10 to 15 minutes until the moisture content of the productwas less than 1%.

Composition F required 3 inversions for full dispersion into a clearsolution.

EXAMPLE 7

This example illustrates the preparation of a 50SG composition(Composition G) of the present invention.

A mixture of 52.0 grams of Flonicamid, 3.0 grams of sodiumalkylnaphthalene sulfonate formaldehyde condensate, 1.0 gram of acombination of sodium dioctylsufosuccinate and sodium benzoate (AerosolOTB available from Cytec Industries, Inc. in West Paterson, N.J.), 41.5grams of lactose and 2.5 grams of a mixture of polyalkyleneoxidemodified heptamethyl trisiloxane and alkyloxypolyethylene glycol methylether (Silwet L-77 available from OSi Specialties, a Crompton Businessin Greenwich, Conn.) were combined and agitated under high shear. Tothis mixture was added 14.0 grams of water and then the mixture waskneaded in a Hobart mixer for about 2 minutes. The kneaded mixture wasthen extruded in a Fuji Paudal DGL-1 using a dome with 0.8-millimeterapertures. The resultant product was then dried at 60° C. with 80%airflow for 10 to 15 minutes until the moisture content of the productwas less than 1%.

Composition G (after being stored at −10 C) required 2 inversions forfull dispersion into a clear solution.

EXAMPLE 8

This example illustrates the preparation of a 70SG composition(Composition H) of the present invention.

A mixture of 72.0 grams of Flonicamid, 5.0 grams of sodiumalkylnaphthalene sulfonate formaldehyde condensate, 1.0 gram of acombination of sodium dioctylsufosuccinate and sodium benzoate (AerosolOTB available from Cytec Industries, Inc. in West Paterson, N.J.) and22.0 grams of lactose were combined and agitated under high shear. Tothis mixture was added 15.0 grams of water and then the mixture waskneaded in a Hobart mixer for about 2 minutes. The kneaded mixture wasthen extruded in a Fuji Paudal DGL-1 using a dome with 0.8-millimeterapertures. The resultant product was then dried at 60° C. with 80%airflow for 10 to 15 minutes until the moisture content of the productwas less than 1%.

Composition H required 3 inversions for full dispersion into a clearsolution.

EXAMPLE 9

This example illustrates the preparation of a 91SG composition(Composition I) of the present invention.

A mixture of 94.0 grams of Flonicamid, 5.0 grams of sodiumalkylnaphthalene sulfonate formaldehyde condensate and 1.0 gram of acombination of sodium dioctylsufosuccinate and sodium benzoate (AerosolOTB available from Cytec Industries, Inc. in West Paterson, N.J.) werecombined and agitated under high shear. To this mixture was added 30.0grams of water and then the mixture was kneaded in a Hobart mixer forabout 2 minutes. The kneaded mixture was then extruded in a Fuji PaudalDGL-1 using a dome with 0.8-millimeter apertures. The resultant productwas then dried at 60° C. with 80% airflow for 5 to 10 minutes until themoisture content of the product was less than 1%.

Composition I required 3 inversions for full dispersion into a clearsolution.

While this invention has been described with an emphasis upon preferredembodiments, it will be obvious to those of ordinary skill in the artthat variations in the preferred compositions and methods may be usedand that it is intended that the invention may be practiced otherwisethan as specifically described herein.

Accordingly, this invention includes all modifications encompassedwithin the spirit and scope of the invention as defined by the claimsthat follow.

1. A soluble granule composition comprising: a) from 45% by weight to55% by weight based upon the total weight of all components in thecomposition of Flonicamid; b) from 2% by weight to 6% by weight basedupon the total weight of all components in the composition of adispersant selected from the group consisting of sodium alkylnaphthalene sulfonate formaldehyde condensate, alkyl naphthalenesulfonate salts and dodecyl benzene sulfonate (Na) salt; c) from 0.5% byweight to 3% by weight based upon the total weight of all components inthe composition of a wetting agent selected from the group consisting ofa mixture of sodium dioctylsulfosuccinate and sodium benzoate whereinthe sodium dioctylsufosuccinate is present in a concentration up to 85weight percent; and d) from 35% by weight to 45% by weight based uponthe total weight of all components in the composition of a water-solublecarrier selected from the group consisting of lactose, sucrose, glucose,starch, sodium tripolyphosphate and water-soluble salts.
 2. Thecomposition of claim 1, wherein the dispersant is sodium alkylnaphthalene sulfonate formaldehyde condensate.
 3. The composition ofclaim 1, wherein the wetting agent is a mixture of sodiumdioctylsulfosuccinate and sodium benzoate wherein the sodiumdioctylsulfosuccinate is present in a concentration up to 85 weightpercent.
 4. The composition of claim 1, wherein the water-solublecarrier is lactose.
 5. The composition of claim 1, further comprising ananti-foam agent.
 6. The composition of claim 1, further comprising ananti-bacteria agent.
 7. A soluble granule composition comprising: a)from 45% to 55% of Flonicamid; b) from 2% to 6% of sodium alkylnaphthalene sulfonate formaldehyde condensate; c) from 0.5% to 3% of amixture of sodium dioctylsulfosuccinate and sodium benzoate wherein thesodium dioctylsulfosuccinate is present in a concentration up to 85%;and d) from 35% to 45% of lactose; wherein all % are % by weight basedupon the total weight of all components in the composition